The Winding Road
by CheeryFan
Summary: While Blair's carefully planned life is on the brink of falling apart, she is more determined than ever to fight for it.  However, a most unexpected ally makes her doubt what she had wanted all along. If she can actually trust him, that is. AU CB with SN.
1. Prologue

**Disclaimer:** I do not own Gossip Girl or any of its characters …this is written purely for fun…sigh… how I wish I did own them though…

Au fic with CB focus but will feature most characters (SN as well).

**Summary:** While Blair's carefully planned life is on the brink of falling apart, she is more determined than ever to fight for it. However, a most unexpected ally makes her doubt what she had wanted all along. If she can actually trust him, that is.

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><p><em><strong>Prologue<strong>_

Nathaniel Archibald was nervous. That, in turn, made Blair Waldorf nervous. Nate was so nervous, that he was practically fidgeting in his seat. Blair had taken one look at her boyfriend standing at the foyer biting his lip and staring intently at the floor and she had immediately realized the gravity of the situation. He had only briefly glanced up when she had come down the stairs and had offered her a hesitant smile and a chaste kiss, turning his eyes downcast almost at once. Blair had swallowed down her growing anxiety and after asking Dorota to bring them some tea, she had graciously led him upstairs to her room.

She had realized since his phone call two hours ago that something was up. Nate had requested rather urgently to see her as soon as possible while he was well aware of the fact that Blair hated rescheduling and they had already made plans to have dinner that same evening. She had assumed it had something to do with his father, as his situation had been going from bad to worse for quite some time now. Not that Nate had been too willing to talk about his father and his troubles, thus far. She had learned more about the rumored scandal from Dorota, who was friends with the Archibald's Ukrainian maid, rather than her tight-lipped boyfriend. Now that Nate seemed inclined to actually talk to her, hardly masking her disbelief and excitement, Blair had graciously accepted the change of plans without uttering a single complaint, willing to support her boyfriend in his hour of need.

But as the time passed and Nate just sat there looking at her bedding as though it was the most fascinating thing in the world, Blair's patience was running out and fast. Dorota had come and gone with their tea and now Nate really did not have any more excuses. Blair had even cleared her throat twice, but that also failed to pull him from his inner thoughts.

"Nate!" She snapped finally with a huff. How could she be an understanding girlfriend if he still refused to talk about his problems? And if he was determined as usual to keep everything to himself, then, why on earth had he called her and forced her to cancel her shopping trip with Jenny?

Nate raised his head startled, looking at Blair like he had forgotten she was actually in the room with him. She just looked at him pointedly. She was seconds away from tapping her foot in impatience.

Nate released a heavy sigh and his expression turned to something between pain and actual fear. He opened his mouth to say something but he snapped it back shut, shaking his head like he was regretting it and turned back to look at the bedding.

Blair was starting to get actually worried, not to mention extremely frustrated. She had been determined to listen to him, but since he did not look forthcoming, she decided on a change of tactics. After all, Nate always needed some gentle prodding to come through for her.

"What's wrong?" she asked trying to valiantly keep both her anxiety and her frustration out of her voice and making it sound more soothing instead. "Is it something concerning your father?" she continued with a sympathetic look.

Nate could not hide a grimace, "Sorta", he mumbled still not looking at her.

"Tell me", Blair insisted trying to tamper down on her impatience as she reached out her hand to squeeze his knee.

Nate sighed again and finally turned his head to actually look at her. His expression seemed now more fearful than before, but Blair could tell he had finally decided to talk. She watched him as he debated with himself for a few more seconds and finally locking clear blue eyes on her wide brown ones, he took a deep breath in and quickly blurted out, "I'm getting engaged."

Blair felt very undignified with her mouth hanging open like this, but there was little she could do about it.

"Wait what?" she asked just to make sure she was not hearing things.

Seeming to have found some well-hidden courage depletes, Nate took another deep breath and this time pronounced much more clearly, "We're supposed to break up, and I'm supposed to get engaged."

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><p><strong>AN:<strong>

I now this is short, but next chapter will follow soon. Hope you enjoyed, and I'd love to hear what you think!

A big thank you goes to all the ladies in _gossip-fic . net_ because without their encouragement, I wouldn't have started writing this at all.

Special thanks to:

**nondescriptf**, because without her organizing writing sessions in my time zone, I wouldn't have written more than one line…

**Kiss of Death** and **KatieDV** for their advices and suggestions in the very beginning of this exploit…

**uncorazonquebrado**, many many thanks for listening to my ranting (we called them ideas…) and for all your brilliant ideas that helped me overcome many of my issues with the story! I could not be more grateful!

And last but not least, **MegamiTenchi**, many thanks for being the world's quickest beta plus researching with me and encouraging me to actually post.


	2. Chapter 1

**Chapter 1**

Three weeks later…

Blair mechanically brought her champagne flute to her mouth, not actually taking even a sip. Her attention was fully devoted to the couple standing at the other side of the wide hall. It was not just her though; a quick look around and one could see that most eyes were focused on the golden couple. The duo commanded everyone's attention; there was a light emanating from them, a brightness that drew one in. Blair watched with fascination how they glided among the people, all dazzling smiles and bright eyes. She on the other hand radiated as much light as moonless night. Dark hair and dark eyes that seemed even darker now as she had practically molded herself to the wall in the secluded corner she had chosen to hide behind.

She could not help the thoughts that swarmed her mind. Nate and Serena made the perfect couple. Right out of a fairytale, the beautiful princess and the handsome prince. They looked like they could be movie stars or royalty, and they fit together perfectly. Everyone, _everyone_ could see that. She wondered if Nate and Serena could see the perfect picture they made, would they also realize what everyone else saw? Blair shivered. Nonsense. Nate loved her. Her. And Serena was not interested in Nate. She was on their side. Still, hidden there in the shadows watching the fair couple, the prince and the princess, who paraded in their pretended bliss, Blair could not help but feel like the wicked witch in _their_ fairytale.

The champagne made it past her lips at last, but the dark thoughts plundering her did not allow for the cool liquid to provide any sort of relief. Lowering the glass, she managed to avert her eyes from the magnetic effect her boyfriend and his soon to be fiancée made. Blair glanced around the rest of the vast hall indifferently, seeing most people either watching the beautiful couple themselves or immersed in their own conversations. Presumably everyone was discussing the photographs showcased all around the room, but in reality, there were only few occasional glances spared at them. In all honesty, the photographs had lost their interest about fifteen minutes after the opening, and now most attendants indulged in their favorite past time activity: gossip.

At least they no longer seem to remember that she was there. The impression her entrance had caused was long forgotten now that she stayed quietly hidden in her corner. As she had not caused a scene, like most probably had hoped for, she was not worth talking about. Not when there were so many more interesting things to discuss at a Van der Bass organized event. Blair sighed and took another small sip of her champagne, marveling at her invisibility. She doubted the Van der Bass princess could ever pass by as unnoticed as she was right now.

But maybe she was not as invisible as she seemed to believe. An uneasy feeling creeping at her back made her look around again trying to trace its source. She was met with a pair of blue eyes, not glimmering like Nate's or brilliant like Serena's. These eyes were icy blue, almost transparent, and their gaze was penetrating and tense. She recognized the impressive man in the Armani suit with the cold eyes right away. Who in Manhattan would not recognize the powerful billionaire? He was Bartholomew Bass, Bart as they called him, and he was looking straight at her.

Blair was not easily intimidated, she was accustomed to wielding power, not cowering from it, but she could not help but glance away instinctively against this man's cold stare. She recovered almost immediately. She was Blair Waldorf and she was not afraid of anyone. Lifting her chin, she had no doubt Bart Bass knew exactly who she was, Blair stared right back at him defiantly even taking a step away from the wall to reveal her self from the shadows. She thought she saw the man actually raise his eyebrows, seeming… impressed? Surprised? Or maybe amused? She could not really tell and he had already turned away as someone had approached to talk to him.

Blair deflated, ready to retreat to her corner when she heard a chuckle coming from her side. Not having realized that anyone was standing that close to her, she swiveled her head, and this time she found a pair of much darker eyes staring back at her. And though they had nothing in common with the icy blue eyes that had stared at her a minute ago, Blair could see how similar they were in their intensity. However, these eyes were dark, almost as dark as her own, with caramel colored, almost golden looking speckles that made them shine in the bright light of the September morning. Blair blinked again to break the hypnotic effect their heated stare had on her and immediately frowned as she recognized their owner. She would have groaned if her manners had allowed it; because there standing beside her and watching her with apparent amusement, was no other than Chuck Bass, Bart Bass' notorious son.

The sole heir of the Bass Empire was as recognizable as his father. It was impossible to live on the island of Manhattan and not know of Chuck Bass. Blair had heard so many stories and so much gossip about his exploits, there could very easily be a book about him! Stories about outrageous parties and reckless escapades. Stories about a cruel, ruthless man that always got what he wanted, just like his father. But most of all, stories about an endless stream of conquests that overstayed their welcome in his bed before the night had even ended. Some of the stories Blair would insist were clearly over-exaggerated, and complete and total nonsense. But she could never be completely sure. That was the thing about the Bass heir, unlike the rest of his family, especially his sister that lived under the spotlight; he was always shrouded in a cloud of mystery. Stalking in the shadows, just like he was doing right now, just like Blair herself had been doing this entire morning.

He still had not spoken to her; he just kept staring at her, with a smirk on his handsome face.

"What?" Blair snapped irritated that he had dared invade her isolation and especially that he had witnessed her stare down with his father.

The young man, who had been leisurely leaning against the wall at her side, now raised himself up as he turned to her. Wearing a wide, charming smile, that Blair felt it was so fake, it seemed like an insult.

"No reason to get testy," he drawled lazily, "I just came to introduce myself."

"Please," Blair rolled her eyes interrupting, "like there was a chance I didn't know who you are."

"You flatter me, Miss..." he trailed off.

"And you, Mr. Bass, insult me if you think I'll believe even for one minute you don't know who I am."

"Please, call me Chuck," he said with a minute grimace, "And don't you mean who you used to be, Waldorf?" He asked as his mouth formed into a smirk again, leading Blair to decide that it must be his favorite facial expression. Or a genetic defect. Still, she did not understand his meaning and narrowing her eyes she suspiciously waited for his explanation.

Not one to disappoint, Chuck hurried to deliver his blow, "Used to be… Archibald's girlfriend?"

Blair commanded herself to remain still and not allow him to see how much that had hurt. "Was there something you wanted, Bass?" she asked warily.

Chuck chuckled, "I was just curious about what you are doing here."

"I was invited," Blair snapped back.

"Hm... Archibald invited his ex-girlfriend to the opening of an art exhibition hosted by the mother of his current girlfriend. Didn't think he had it in him..." he mused.

"Your sister was actually the one that invited me," Blair clarified with a fake smile of her own. She had no idea how much about the situation Chuck Bass actually knew and she damned Nate for not letting her know in advance whether he was in with their plot or not. She had to be very careful with him, Bass' entire demeanor screamed danger. Or it could just be that she was really apprehensive about him based on all the things she had heard.

Chuck did not seem surprised by her remark, just amused again, and Blair was growing frustrated. She was not going to be seen as a means for his entertainment, especially when she felt like crying.

"Really? How gracious of her," Chuck continued unaware of her inner thoughts as she had schooled her face to remain impassive. "But that still doesn't answer why you accepted the invitation."

Blair's mouth tightened in a line, damn him for keep prodding. Did he actually know what was going on and just enjoyed torturing her or was he becoming suspicious? Would the golden princess have confided on her stepbrother? Was he on their side? He could be, he was Serena's stepbrother, but he was also Bart's son. Blair had to tread carefully.

"Why wouldn't I? We are all civilized people; Nate and I have known each other since preschool. I see no reason for us to not remain friends just because-"

"Just because he left you high and dry?" Chuck interrupted her, "left you for bigger and better things?" he insinuated suggestively tilting his head in the general direction of his stepsister and Nate.

Blair could not hide her flinch this time. "You're disgusting," she hissed and turned away from him. She loathed leaving the refuge of the shadowy corner and enduring the curious and pitiful looks that had made her seek it out in the first place. Nevertheless, staying in this conversation for a minute longer was not something she could afford.

Chuck, however, was not to be so easily deterred and followed her into the light. They were no longer hidden and Blair could already see that some of the other attendants had now turned their attention from the golden couple to Chuck and her. She wondered what they were thinking, at least now they looked more curious than sorry for her. She stopped and turned to face the annoying young Bass that had remained at her side. "Do you not understand that I do not wish to speak with you any longer?"

Chuck merely smirked and Blair had to actually fight the urge to slap it off his face. How could someone be so annoying? And how on earth had he managed to acquire a reputation as a suave womanizer? Of course, Blair realized, he probably would not be pestering her this way if he was interested in her like that. He could probably be very charming, had he wanted to be. Standing next to him certainly was a bit disarming, she begrudgingly admitted to herself. He was even more attractive in person, radiating a heat that the photos she had seen could never emanate. She had to fight the urge to inspect her own appearance. After much deliberation, she had settled for a black pencil skirt that reached just past her knees and a satin long sleeved blouse with a ruffled neck in deep peach. Black heels and a headband adorning her carefully combed curls completed her look. She knew it was nothing special. A man like Chuck Bass was not interested in girls in pencil skirts and blouses that covered all her assets. She had seen enough photos of the women that claimed he had graced their bed to know she was certainly not his type. So why would he be charming to her? Instead, he opted for showing her his spoiled brat side, she thought with a frown.

"You shouldn't be so hard on me, I'm only trying to help you, after all," Chuck finally replied.

"Help me?" Blair could not help the incredulity in her voice. "How pray tell do you think you're helping me? By insulting me, perhaps?" She hissed but managed to keep her voice level, she did not want to attract any more attention. It was bad enough she was not hiding any more.

Chuck merely rolled his eyes, "I thought you would be smarter than this, Waldorf."

Blair bristled but at the same time felt extremely unnerved. Did he or did he not know? The way he acted was confusing. On one hand, if he did know and he was only messing with her, Blair would feel like a fool. On the other hand, she could not afford to slip up and reveal something she should not. In other words, she could not handle Bass if she did not know how much he knew. She had to play it safe. "Are you helping me again?" she asked him sarcastically raising an eyebrow.

"For one, you no longer look like the pathetic ex-girlfriend hiding in the corners," Chuck deadpanned.

Blair's mouth formed into a perfect 'O'.

"Now," Chuck continued, "close your pretty little mouth and come with me to get another drink."

Before she had time to answer Blair felt his arm sneak behind her and come to rest at the small of her back. The contact was jarring and for a second Blair had to question whether her blouse actually covered her back as the thin silk seemed inadequate from keeping the heat of his fingers from scorching her skin. She wanted to fight him, but she had to agree with him. She had been looking rather pathetic thinking that she could hide from the onlookers. Blair Waldorf did not hide. Not from anyone or anything. When Jenny had warned her that it would be like this, was she not the one that told her that a Waldorf woman would never look pathetic? She was not going to cause another scene, and if anyone was going to look at her from now on, it was not going to be with pity.

So Blair let herself be guided to the bar by the younger Bass. Looking around she could see that more and more people turned their attention to them now. It was actually quite satisfying; the thought that she could make people turn away from the fair princess to actually look at her. Of course, the man walking with her had a lot to do with this. Blair scoffed for a minute; did people think he was trying to stop her from causing a scene? Would they be thinking that he was trying to get the psychotic ex away from his sister?

As they reached the bar, Chuck removed his hand and turned to order himself a scotch and another champagne for her.

"What do you think I look like know?" Blair could not resist asking him as he handed her a new flute.

Chuck smiled, "You look gorgeous," he offered letting his eyes roam from her head to her shoes.

Blair rolled her eyes, though she had to admit, she enjoyed the compliment especially because of the way his eyes taking her in made her believe he truly meant it. Despite her less than revealing or flashy appearance. It was now becoming easier to understand how he had acquired his fame as the Upper East Side's irresistible playboy.

"You know what I mean," she insisted trying to get him to answer her original question. Instead of letting him corner her all the time, Blair decided it was time she pushed him to reveal his true intentions. She had to figure out how much he knew about the tangled web they were weaving. He might be as manipulative and smart as his father, but Blair was not new to this sort of games, and both Bass men would discover this soon enough.

Chuck just smiled serenely, drinking his scotch and letting his eyes wander as he casually leaned back against the bar. There was nothing casual about him though. Blair followed his eyes and saw how deliberately he was seeking out his sister and Nate. They were glancing their way at the moment and Blair could finally read both of their expressions, seeking the answer she desperately needed. No Chuck was not supposed to know anything about their agreement. Both blondes mirrored the same expression of shock and high anxiety. Now, Blair felt more comfortable, even though she knew she had to be even more careful. But at least she knew where she was standing, and knowledge was power as she had explained numerous times to her minions.

"Your sister doesn't look too happy that you decided to _help_ me," she stressed sarcastically.

Chuck grinned, "Neither does your ex-boyfriend."

"I would assume it is because they are both unable to understand your reasons. As am I," Blair continued.

Chuck shrugged, "Would you believe it if I said that I was just being a gentleman?"

Blair scoffed in disbelief.

"I was bored..." Chuck drawled eventually.

"And you thought torturing the poor ex-girlfriend was a nice pastime?"

"Tsk, Tsk, Waldorf," Chuck reprimanded easily, "I am not the one you should blame for that. You are the one that came here, and I want to know why," he finished seriously and his eyes stared at Blair intensely.

Blair bit the inside of her cheek; of course she would be raising suspicions. She had known it was still too early to come, she knew it would have been better if she had not. She knew but she could not stop herself from coming. She had to see them together. She had to be there. For the two weeks they had started "dating", she hated not knowing what was going on when they were out together. Nate assured her it was mostly them discussing the details of their plan, but Blair was not interested in what they were saying. For some reason she could not quite identify, she had wanted to see them together. Actually _see_ how the two of them looked together. She had known she would not like it, but the need was too great to resist.

When Bart Bass had looked at her she knew he was not happy about her being there, but she knew he was not about to cause a scene and attract more attention to her by approaching her. She had not expected the younger Bass to be the one that came to her. This thought made her search for the older Bass in the crowd. She did not have trouble locating him; he was seemingly absorbed into conversation, his striking wife by his side smiling radiantly. Like mother, like daughter, she thought bitterly. Lily Bass was every bit as impressive and striking as her daughter. Only Blair was never able to be as strong and confident as her own mother.

Looking at Lily however, Blair caught Bart subtly looking their way. He did not look happy.

Blair looked back at Chuck to see him watching his father as well. His eyes were hard and as though he could feel her looking at him, he turned to her, letting some of the intensity leave his eyes.

"Aren't you going to tell me why?" he insisted and Blair had no idea what she could say when she heard another voice behind her.

"Chuck," someone called attracting both their attentions. Blair squinted slightly at this new arrival, a younger man, with light brown hair and much lighter looking eyes was smiling at them warmly. It took her a second, but she finally realized who the other boy was- Serena's Van der Woodsen younger brother, Eric - just as Bass was greeting him. Was she doomed to meet the entire family today? She certainly had not come prepared for that and now she cursed herself for her naivety.

"Eric, you made it, I see," Chuck said and Blair noticed that his face seemed the most relaxed she had seen him so far. This only served to confirm that Chuck Bass had been on the guard with her this whole time.

Eric nodded vigorously, "Thank you for sending Arthur to get me."

Chuck shrugged it off, and then making an exaggerated attempt to show that he had just remembered her presence, turned back to Eric. "Eric, I don't think you've met Blair before."

She was quite taken aback to hear him call her with her first name. So far, he had only called her Waldorf, though he had shown to take particular pleasure in referring to her as the 'ex-girlfriend'.

Eric had smiled at her, when Chuck continued with his introduction making the smile vanish from the younger boy's face. "She's a very dear friend of Nathaniel's," he paused with a smirk, "and Blair, this is my favorite stepbrother, Eric."

The younger boy still had not recovered from the shock. Apparently, he had not recognized her until a minute ago. Blair just smiled, suppressing the need to kick the Basshole for the way he ambushed his brother. "Nice to meet you, Eric," she offered.

"Likewise," Eric replied throwing a not so subtle look at Chuck, obviously wanting to know what the hell was going on.

"Well, now that you have company, and you won't be bored anymore, I think it is time I took my leave," Blair suggested taking the opportunity to get away from the insistent man, before the rest of the Van der Bass family thought it appropriate to come and introduce themselves.

Eric did not even try to hide his eagerness, obviously seeing this as an opportunity to question his brother about her. Chuck however raised himself from the bar, nodding. He stepped quickly beside her in a move she did not have time to counter and his arm again sneaked around her waist. To her dismay and surprise the effect his fingers had on her skin was exactly the same.

"Eric," he addressed the other boy at the same time, "I will be back shortly, just allow me to escort Blair out."

Eric nodded bewildered, and Blair herself was beyond surprised that she was not actually arguing with him, though he had hardly given her the time to do so. She found herself being led by him for the second time that day and as they made their way out, the whispers around them intensified. Blair stiffened wondering again if everyone was thinking about how Chuck was rescuing his sister by escorting the psychotic ex-girlfriend out. What bothered her even more was the thought that Bass himself might be thinking the exact same thing. Was this his agenda all along? Was he afraid she was going to cause a scene and he was trying to prevent it? She did not have time to think more of it because they had reached the foyer and Chuck was commanding the personnel to bring Blair's coat.

She stepped out of her stupor when the coat was presented to her.

"Well, you have seen me out, now you can go back sure that I am not going to ruin your family's event."

Chuck's eyes narrowed for a second, "I can tell you're smarter than that, Waldorf."

Blair did not look convinced. "You didn't think I was smart earlier," she replied.

Chuck frowned, "It was not smart coming here and I know you know that."

Blair did not reply, as she could not deny the truth in his words. She knew it herself but she had not been able to stop herself. It was stupid of her.

"Goodbye, Bass," she said instead, deciding that at least running away now was the smart thing to do.

His hand on her arm stopped her. "You haven't answered my question, yet."

Blair gently retracted her arm back as his intention had been only to get her attention and not actually stop her from leaving. Blair was just glad she had already put on her coat. At least the heavy cashmere was able to protect her from the heat of his touch much better than her flimsy silken blouse had.

"You didn't really answer mine either," she countered not missing a beat.

Chuck smiled looking satisfied with her retort, "Until next time, then?" he offered.

Blair just huffed and turned around quickly walking away. Something told her that next time would be coming too soon for her liking. At least next time the Basstard was not going to catch her unprepared.

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><p><strong>AN:<strong> Many many thanks and love to my beta MegamiTenchi, I am so lucky to have her! And much love and thanks to everyone that read, reviewed, favored or put this fic in their alerts!

I would love to hear what you thought of this chapter, and sorry for not putting it out there sooner! I hope it didn't seem too confusing, though a bit, it's okay! All will become clear in time :)


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